Tributylphosphine → HCID 68242824, compound

HRID 1844575Notes

Reaction equation

HRID 1844575 reaction equation
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[Si:19]([O:36][CH2:37][CH2:38][C@@H:39]([CH3:42])[CH2:40]O)([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH:43]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45].C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CCCCCC>[Si:19]([O:36][CH2:37][CH2:38][C@@H:39]([CH3:42])[CH2:40][N:43]([C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])([C:32]([CH3:33])([CH3:34])[CH3:35])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 279800Di-tert-butyl IminodicarboxylateHCID 11210066HCID 11210066, compound

Product 1

HCID 68242824HCID 68242824, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

1,1′-(Azodicarbonyl)dipiperidine (6.33 g) was added to a solution of (2R)-4-{[tert-butyl(diphenyl)silyl]oxy}-2-methylbutan-1-ol (Synthesis, 2002, p. 1993) (4.30 g), di-tert-butyl iminodicarboxylate (5.45 g), and tributylphosphine (4.65 mL) in toluene (130 mL) with stirring at 0° C. The mixture was heated to room temperature and stirred overnight. Then, the reaction solution was diluted with hexane, and insoluble matter was filtered off through celite. The filtrate was concentrated under reduced pressure, and the obtained crude product was then purified by silica gel column chromatography to obtain the title compound (3.86 g).

Workup

  1. temperatureThe mixture was heated to room temperature
  2. stirringstirred overnight
  3. filtrationwas filtered off through celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe obtained crude product
  6. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-32ee09e1afbf4e58a44aaea9812ef6aa
Source dataset
uspto-grants-2015_02
Patent number
US08946443B2

Reaction notes

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